KR102609305B1 - 1,2,4,5-시클로헥산테트라카르본산이무수물의 제조방법 - Google Patents
1,2,4,5-시클로헥산테트라카르본산이무수물의 제조방법 Download PDFInfo
- Publication number
- KR102609305B1 KR102609305B1 KR1020197027646A KR20197027646A KR102609305B1 KR 102609305 B1 KR102609305 B1 KR 102609305B1 KR 1020197027646 A KR1020197027646 A KR 1020197027646A KR 20197027646 A KR20197027646 A KR 20197027646A KR 102609305 B1 KR102609305 B1 KR 102609305B1
- Authority
- KR
- South Korea
- Prior art keywords
- cyclohexanetetracarboxylic
- cyclohexanetetracarboxylic acid
- acid
- particle diameter
- particles
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 44
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000002245 particle Substances 0.000 claims abstract description 136
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 claims abstract description 83
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 25
- 239000002002 slurry Substances 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims description 57
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- 238000006297 dehydration reaction Methods 0.000 claims description 30
- 239000002994 raw material Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 21
- 238000001035 drying Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 71
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 34
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- 239000012141 concentrate Substances 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000004811 liquid chromatography Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000012159 carrier gas Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- -1 Alicyclic acid anhydrides Chemical class 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017065899 | 2017-03-29 | ||
| JPJP-P-2017-065907 | 2017-03-29 | ||
| JPJP-P-2017-065899 | 2017-03-29 | ||
| JP2017065907 | 2017-03-29 | ||
| PCT/JP2018/011331 WO2018180854A1 (ja) | 2017-03-29 | 2018-03-22 | １，２，４，５－シクロヘキサンテトラカルボン酸二無水物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20190136000A KR20190136000A (ko) | 2019-12-09 |
| KR102609305B1 true KR102609305B1 (ko) | 2023-12-05 |
Family
ID=63675817
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197027669A KR20190133676A (ko) | 2017-03-29 | 2018-03-22 | 1,2,4,5-시클로헥산테트라카르본산이무수물의 제조방법 |
| KR1020197027646A KR102609305B1 (ko) | 2017-03-29 | 2018-03-22 | 1,2,4,5-시클로헥산테트라카르본산이무수물의 제조방법 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197027669A KR20190133676A (ko) | 2017-03-29 | 2018-03-22 | 1,2,4,5-시클로헥산테트라카르본산이무수물의 제조방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US11174269B2 (zh) |
| EP (2) | EP3604313A4 (zh) |
| JP (2) | JPWO2018180855A1 (zh) |
| KR (2) | KR20190133676A (zh) |
| CN (2) | CN110461851A (zh) |
| TW (2) | TWI785025B (zh) |
| WO (2) | WO2018180854A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110461851A (zh) * | 2017-03-29 | 2019-11-15 | 三菱瓦斯化学株式会社 | 1,2,4,5-环己烷四羧酸二酐的制造方法 |
| CN114163449B (zh) * | 2021-12-20 | 2023-03-17 | 大连奇凯医药科技有限公司 | 1,2,4,5-环己烷四羧酸二酐的制备及表征方法 |
| TWI800442B (zh) * | 2022-08-15 | 2023-04-21 | 中國石油化學工業開發股份有限公司 | 1,2,4,5-環己烷四甲酸之純化方法 |
| CN115894512A (zh) * | 2022-12-21 | 2023-04-04 | 大连奇凯医药科技有限公司 | 一种1,2,4,5-环己烷四羧酸二酐的合成及检测方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006083080A (ja) * | 2004-09-15 | 2006-03-30 | New Japan Chem Co Ltd | 水素化芳香族ポリカルボン酸の製造方法 |
| JP2006124313A (ja) * | 2004-10-28 | 2006-05-18 | Nippon Steel Chem Co Ltd | 脂環式多価カルボン酸及びその無水物の製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53103437A (en) * | 1977-02-21 | 1978-09-08 | Mitsubishi Rayon Co Ltd | Continuous feed of slurry |
| JP3523419B2 (ja) * | 1996-06-12 | 2004-04-26 | 株式会社クラレ | 微粒子分散性に優れたポリエステルの製造方法 |
| EP1323700B1 (en) * | 2001-12-28 | 2007-08-22 | Mitsubishi Gas Chemical Company, Inc. | process for producing hydrogenated aromatic polycarboxylic acid and process for producing hydrogenated aromatic polycarboxylic anhydride |
| JP4633400B2 (ja) * | 2004-08-09 | 2011-02-16 | 新日鐵化学株式会社 | 脂環式多価カルボン酸及びその酸無水物の製造方法 |
| CN105418405A (zh) | 2008-07-23 | 2016-03-23 | 三菱瓦斯化学株式会社 | 芳香族多羧酸的加氢化合物的制备方法 |
| CN103992330B (zh) | 2014-05-23 | 2016-09-21 | 常州市阳光药业有限公司 | 电子级氢化均苯四甲酸二酐的制备方法 |
| CN104926649B (zh) | 2015-05-20 | 2016-08-24 | 大连奇凯医药科技有限公司 | 氢化均苯四甲酸四丙酯和1,2,4,5-环己烷四甲酸二酐的制备方法 |
| CN110461851A (zh) * | 2017-03-29 | 2019-11-15 | 三菱瓦斯化学株式会社 | 1,2,4,5-环己烷四羧酸二酐的制造方法 |
-
2018
- 2018-03-22 CN CN201880018816.3A patent/CN110461851A/zh active Pending
- 2018-03-22 EP EP18774234.1A patent/EP3604313A4/en not_active Withdrawn
- 2018-03-22 US US16/496,697 patent/US11174269B2/en active Active
- 2018-03-22 JP JP2019509647A patent/JPWO2018180855A1/ja active Pending
- 2018-03-22 KR KR1020197027669A patent/KR20190133676A/ko not_active Application Discontinuation
- 2018-03-22 JP JP2019509646A patent/JP7196835B2/ja active Active
- 2018-03-22 CN CN201880018837.5A patent/CN110494437A/zh active Pending
- 2018-03-22 WO PCT/JP2018/011331 patent/WO2018180854A1/ja unknown
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- 2018-03-22 WO PCT/JP2018/011333 patent/WO2018180855A1/ja unknown
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- 2018-03-26 TW TW107110182A patent/TWI785025B/zh active
- 2018-03-26 TW TW107110181A patent/TWI786098B/zh active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006083080A (ja) * | 2004-09-15 | 2006-03-30 | New Japan Chem Co Ltd | 水素化芳香族ポリカルボン酸の製造方法 |
| JP2006124313A (ja) * | 2004-10-28 | 2006-05-18 | Nippon Steel Chem Co Ltd | 脂環式多価カルボン酸及びその無水物の製造方法 |
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|---|---|
| US20200031841A1 (en) | 2020-01-30 |
| JP7196835B2 (ja) | 2022-12-27 |
| TW201840524A (zh) | 2018-11-16 |
| CN110461851A (zh) | 2019-11-15 |
| JPWO2018180855A1 (ja) | 2020-02-06 |
| TW201840523A (zh) | 2018-11-16 |
| TWI785025B (zh) | 2022-12-01 |
| TWI786098B (zh) | 2022-12-11 |
| WO2018180854A1 (ja) | 2018-10-04 |
| US20200039999A1 (en) | 2020-02-06 |
| EP3604314A4 (en) | 2020-02-05 |
| JPWO2018180854A1 (ja) | 2020-02-06 |
| EP3604313A1 (en) | 2020-02-05 |
| EP3604313A4 (en) | 2020-02-26 |
| KR20190133676A (ko) | 2019-12-03 |
| KR20190136000A (ko) | 2019-12-09 |
| WO2018180855A1 (ja) | 2018-10-04 |
| CN110494437A (zh) | 2019-11-22 |
| US11174269B2 (en) | 2021-11-16 |
| EP3604314A1 (en) | 2020-02-05 |
| EP3604314B1 (en) | 2022-02-23 |
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